Dolphin Challenge Cup
Presented anonymously in 1966 as a points trophy for slow handicap racing, but now re-allocated and awarded as the trophy for one of the general handicap special events.
| Year | Helm | Crew | Class | Sail number | Boat name |
| 1966 | HR Kindersley | Kestrel | 301 | Steady Girl | |
| 1967 | AE Monk | Wayfarer | 968 | Spinaway | |
| 1968 | AE Monk | Wayfarer | 968 | Spinaway | |
| 1969 | HR Kindersley | Kestrel | 301 | Steady Girl | |
| 1970 | S Raven | 505 | 3737 | Easy Rider | |
| 1971 | JSW Locke | 505 | 3873 | The Thrashing Machine | |
| 1972 | JSW Locke | 505 | 4432 | Miss Hit | |
| 1973 | EB Raybould | Kestrel | 456 | Moby Dick | |
| 1974 | FNM Pusinelli | Solo | 1312 | Noloa | |
| 1975 | WB Mansell | Laser | 12283 | K2 | |
| 1976 | WB Mansell | Laser | 12283 | K2 | |
| 1977 | Mike Powell | Laser | 41311 | Delicious II | |
| 1978 | Mike Powell | Laser | 54481 | Rockalaser Baby | |
| 1979 | Mike Powell | Laser | 54481 | Rockalaser Baby | |
| 1980 | Jonathan Townsend | Wayfarer | 6288 | Devon Pickle | |
| 1981 | Jonathan Townsend | Wayfarer | 6288 | Devon Pickle | |
| 1982 | Chris Treagust | Laser | 7297 | Imalone | |
| 1983 | Guy Durham | Albacore | 1837 | Rusty Miss | |
| 1984 | Jonathan Townsend | Wayfarer | 6288 | Devon Pickle | |
| 1985 | Roger Bleasby | Wayfarer | 6494 | Masquerade | |
| 1986 | C Morgan | Solo | 3404 | The Mohock | |
| 1987 | RT Groom | Laser II | 2038 | Overdraft | |
| 1988 | RB Lang | Wayfarer | 3396 | Hubbub | |
| 1989 | RT Groom | Laser II | 2038 | Overdraft | |
| 1990 | Jonathan Townsend | Osprey | 1241 | The Innocent | |
| 1991 | G Swift | Laser II | 8304 | Bora Bora | |
| 1992 | Phil Poyner | Jill Poyner | Laser II | 8306 | |
| 1993 | John Davis | Wayfarer | 981 | Rebecca | |
| 1994 | Simon Baber | Albacore | 7145 | Hitch Hika | |
| 1995 | Tim Weeden | Mel Millar | RS400 | 415 | |
| 1996 | Phil Mant | Albacore | 7518 | Reckless Rat | |
| 1997 | Tim Weeden | Mel Millar | RS400 | 548 | Strimmer |
| 1998 | Tim Weeden | Mel Millar | RS400 | 548 | Strimmer |
| 1999 | Tim Weeden | Mel Millar | RS400 | 548 | Strimmer |
| 2000 | Not sailed - weather | ||||
| 2001 | Anthony Reeves | Laser | |||
| 2002 | Simon Townsend | Annie Porter | RS400 | ||
| 2003 | Simon Baber | Albacore | 7145 | Hitch Hika | |
| 2004 | Matt Best | Laser | 130158 | ||
| 2005 | Trevor Newley | Giles Bowman | Wayfarer | 998 | |
| 2006 | Joe Burnie | RS400 | 973 | ||
| 2007 | Trevor Newley | Giles Bowman | Wayfarer | 998 | |
| 2008 | Simon Pettit | Finn | 573 | ||
| 2009 | Simon Townsend | Ben Townsend | National 12 | 3429 | Billy the Hoover |
| 2010 | Matthew Townsend | ||||
| 2011 | Trevor Newley | Giles Bowman | Wayfarer | ||
| 2012 | Vikki Payne | Stephanie Orton | 29er | 1960 | |
| 2013 | Vikki Payne | Stephanie Orton | 29er | 1960 | |
| 2014 | Dave Acres | RS300 | 480 | ||
| 2015 | Jonathan Townsend | Barbara Langford | 2000 | 21431 | Jambo II |
| 2016 | Tom Tredray | RS Aero 9 | |||
| 2017 | David Patterson | Contender | 693 | ||
| 2018 | Ben Oakley | Devoti D-Zero | 176 | ||
| 2019 | Gareth Tweedle | Europe | 406 | ||
| 2020 | Not sailed - COVID-19 | ||||
| 2021 | Patrick Bonner | Laser | 216001 |